This paper illuminates how the psychoanalytic work of Winnicott and Wittgenstein's philosophy on language complement each other in elucidating a “psychoanalytic language game”. The paper takes a close look at the grammar and linguistic mechanisms which underlie psychoanalytic work. Wittgenstein's linguistic turn from positivism is discussed; his ideas like ‘family resemblance’, ‘aspect seeing’ and ‘language games’ are examined in order to shed light on the paradoxical communication at play in Winnicott's potential space. The paper looks at the potentiality central to therapeutic work, arguing that it accords with what Wittgenstein calls the grammatical optative mode, as Freud already indicated in his theory of dreaming.